


First Dates

by criesinenochian



Category: Supernatural
Genre: Adorable Dean Winchester, Cute Castiel/Dean Winchester, Drabble, I Wrote This Instead of Sleeping, I'm Bad At Tagging, M/M, Short & Sweet
Language: English
Status: Completed
Published: 2019-03-05
Updated: 2019-03-05
Packaged: 2019-11-12 04:17:04
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,819
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18003659
Author URL: https://archiveofourown.org/users/criesinenochian/pseuds/criesinenochian
Summary: Basically Sam is trying to find Dean someone to love before Valentine's Day.





	First Dates

**Author's Note:**

> This is my first fanfic so sorry if it sucks  
> // and this is like the worst drabble EVER (super sorry if you find mistakes!!)

Dean is slowly pushed into a bar, a blindfold wrapped rightly around his eyes, all thanks to Sammy. Valentine's Day is five days away and there is no way that Dean will spend it alone. Again. Sam swears to find him a love interest before the treacherous holiday approaches. 

The smell of liquor and sorrow fills Dean's nostrils the second they step foot in the surprisingly quiet bar. Sam sits him down in a cushiony booth and finally unties the blindfold. 

"Jesus, Sammy, you could've just walked me in by luring me with pie or something. But a blindfold?.. This better be worth my time." Dean grumbles, leaning back into the seat and crossing his arms. Sam sits across from him and smiles, lacing his fingers together on the somewhat sticky table in front of them.

"It will be.. Promise." He says. 

"So what're we doing here? You said it was damn important but what is it? A demon?" He questions. Sam licks his lips and looks around the bar, avoiding Dean's eyes. All sorts of people filter in and out of the bar, tall men with resting frowns, short women desperately looking for a hookup, lonely guys drowning themselves in tears and whiskey, and so on. Sam finally looks back at Dean. 

"I've set you up on seven dates. Five girls and.. Two guys. Don't be mad. I just don't want to see you wallow again this year on Valentine's Day, Dean." He rambles on, explaining how this is a good thing. Dean thinks of all the ways he can kill him. 

"You did what, Sammy?" He leans on the table with his elbows, knitting his eyebrows together with each passing second. 

"Don't get mad- oh, one of them is here now. Be nice!" Sam shouts back at him as he gets up and sits at a far away seat by the bar. Dean abruptly stands up but freezes as a short blonde walks up to his table, brown eyes and a nice figure. 

Maybe these dates aren't going to be so bad... 

"Dean? Its Jo.. Hi." She smiles and holds her hand out for him to shake. Dean sits back down and grabs her hand, shaking gently. The girl takes a seat across from him and slides her purse off her arm. 

She waits for a conversation starter but instead just sits there, hopelessly looking around every few seconds. 

"So, how's your dog doing?" Jo asks enthusiastically. Dean flattens his chin and widens his eyes, pretending to think about her question when in reality, he does not even have a dog. 

"Um, she's.. Sick. Yeah, she got the flu or something bad like uh, that." Dean finishes and waves a waiter over to the table. Jo furrows her brows at him and opens her mouth to speak but gets cut off by the waiter. Dean is more than happy to order a beer. 

"Yes, I'll have a beer and for her.. Do you want a beer? Some wine?" He asks, ignoring her obviously confused face. She scoffs and grabs her purse, scooting out the booth. She struts out of the bar and slams the door behind her, leaving Dean puffing his cheeks and avoiding the waiters glare. 

After a few seconds Sam comes over and gapes at him. 

"What did you do? Dean! Be nice!" He shouts. Dean sighs and throws his hands up in defeat and confusion. 

"I asked her what she wanted to drink and she threw a fucking temper tantrum! How is that bad, Sammy?" He asks. Sam shrugs and waits with him before another girl walks through the door, glancing around, looking for Dean. 

"Okay, this time, be interested and nice! No excessive drinking either!" He calls out before slithering back to his seat at the bar. Dean runs a hand through his hair and locks eyes with who he thinks is the girl, making her come towards his booth. 

"Dean, right? I'm Lisa.." The dark haired brunette politely introducing herself. Dean smiles and waves his hand towards the seat. Lisa giggles and slides into the cushioned spot, situation herself comfortably. 

"So, first dates, huh?" She smiles and tucks some hair behind her ear, glancing up at Dean and then at the table. He smiles. 

"Awkward, right?" 

"Exactly! Like what to say, what is too detailed, when to stop talking.. Ugh." They both smile at each other, him admiring the way her face shines even in the dim lighting of the bar. Her ivory teeth beaming when she smiles, her soft brown eyes gleaming, everything. In this moment, Dean doesn't hate Sam that much anymore. 

"You're gorgeous, Lisa.." He states. 

She laughs and uses her hands to show off her face in a cute way. Dean chuckles at her quirky motions. 

"Here's my number, if you want.." Lisa smiles and scribbles down her digits on a scrap piece of napkin. She slides it across the table and he flips it around and scans over it before shoving it in his pocket. 

"So, if you could be anything, what would you be?" She questions. Hours go by, discussions, questions, jokes, everything was shared between the two. Sam watches from afar and smiles, canceling a few dates to let him basque in the joy of being with someone. He scheduled one person per hour, so now Dean only has two people left if he wants. One girl and one guy. 

"Alright, Dean, I think I've hit my wall. But we definitely need to hang out again.. You have my number so I expect a call or text or whatever... Okay, bye." She giggles from having a little too much to drink and stupidly fumbles out the booth. 

"Bye, Lisa!" He calls after her, sitting contently once she leaves. 

Sam walks up to the table and rests his knuckles on the flat surface, grinning down at his brother. Dean chuckles and rubs his eyes, keeping the smile plastered on his face. 

"There's two more people coming in if you wanna see them.. I can cancel also." He states. Dean shakes his head. As happy as he is right now, it never sticks. He can never be too sure. Sam nods and sits down, watching out for either of the other two. 

About twenty minutes go by when a dark haired man walks into the cozy bar, a loose sweater draping across his shoulders. 

"Oh, Dean, I think that's him. The guy. I forgot his name but I trust you to be smooth and find it out. I'll be over there. Good luck." He says and combs through his hair as he leaves Dean at the booth for the third time this night. 

"Dean?" The man calls out to him. He looks over and scans his face. The gems he has for eyes, the rosey film over his lips, his confused eyebrows, his messy and ruffled hair. Whatever he felt for Lisa has heightened by a million. The man walks over to Dean's booth and sits down, gulping nervously. Dean smiles and shakes his hand. 

"You.. Uh, hey." Dean stammers, holding onto his hand a little longer than necessary. The handsome stranger smiles back at him and sets his hands back into his lap, sitting uncomfortably. 

"It's Cas. Castiel Novak. Yeah, I know, what an odd name but it was my mom's idea.. So. Yeah." Dean's mouth is slightly parted and he admires Castiel's everything. His adorably gorgeous face, slender yet fit body, piercing eyes... He can't stop looking at him, which is making Cas slightly anxious. 

"So, Dean, are you some weird serial killer with gross fetishes?" Castiel asks, smiling at his joke. Dean laughs and shakes his head no. 

"Nah, I'm a hunter.. The cool kind, though.. How about you? What do you do?" Dean leans forward on the table, showing immense interest. Castiel smiles and scratches his neck, showing off his defined jawline. 

"I work at a bakery. Have for like three, four years.. Its over by the-"

"Best Buy. Yeah, I've driven past it before.." Castiel nods. Dean taps his finger against his beer bottle, still looking at Cas with astonished eyes. 

"Is this like a hookup or an actual date? You didn't really specify.." Cas trails off. Dean's eyes go wide, he didn't expect Castiel, or anyone, to bring up hooking up even though it would be nice.. 

"I believe it's a date.. Unless you, um... Yeah." Dean stumbles over his words, his tongue suddenly feeling too thick to pronounce proper words. Castiel smiles small, barely noticeable, making Dean grin and take a swig of his beer, never breaking eye contact with Cas. The two men stare curiously at each other and Dean makes it his duty to memorize this angelic man's face. 

Castiel drops his eyes and smiles as he fumbles with something in his pocket. Dean assumes it's his phone, and Cas is looking for any excuse to leave. 

"Put your number in my phone." 

"What?" He asks, barely hearing Castiel at all, his thoughts drowning out sound. 

"I want you to put your number in my phone. So I can call you. Or text you. Or stare at it late at night and smile at the thought of you." Cas trails off as Dean chuckles and holds his hand out for Cas' phone. 

Dean flips it around and starts tapping something on the screen and Castiel watches the small smirk grow on his face, bringing out savory dimples. His eyes remind Cas of emerald gems, his laugh a symphony Castiel could never get tired of listening to. Perhaps it's too early on to feel such strong feelings but damn. He hopes this date is anything but ephemeral. 

"There. Now, if I don't answer it's probably 'cause I'm out saving people, hunting things, ya know. That kind of stuff.." Dean states. He plasters on a tough fop face and then laughs, taking a small swig of his beer. Cas adjusts his sleeves and nods, grinning too. 

Time flies by. The two men sit in that booth and laugh and talk and connect. Dean had never really had a decent love interest or really anyone because if his time consuming job. Cas on the other hand, he's dated many guys but none have ever truly bonded with him. Not like Dean has. From afar, Sam glances over and smiles to himself, finally able to see his brother happy. 

"Well, hello to you, sailor.." A man speaks up next to Sam. Sam turns his head and smiles, now turning his whole body. This stranger has combed over brown hair and soft dips of honey for eyes. Sam gulps. 

"I'm Gabriel. And you are?" He asks, twirling the tiny umbrella in his girly drink. Sam combs a hand through his hair then holds it out for the other man to shake. 

"Sam. My name is Sam." 

xx

T h e E n d .


End file.
